3256-38-0

Usage

Class

Benzenemethanols/ Phenylmethanols

Classification

Phenolic compound

Structure

Contains a hydroxyl group attached to a benzene ring

Identifying group

Hexyloxy group (six-carbon chain attached to benzene ring)

Common uses

Production of plastics, solvents, fragrances

Potential applications

Pharmaceuticals, agrochemicals

Upstream product

• 111-25-1 1-bromo-hexane 
• 123-08-0 4-hydroxy-benzaldehyde 
• 638-45-9 1-Iodohexane 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 50822-54-3 methyl 4-hexyloxybenzoate 
• 5736-94-7 4-(hexyloxy)benzaldehyde 

Downstream Products

• 56922-67-9 1-(chloromethyl)-4-(hexyloxy)benzene 
• 155929-56-9 3,4,5-tris(p-hexyloxybenzyloxy)benzoic acid 
• 155929-62-7 3,4,5-Tris-(4-hexyloxy-benzyloxy)-benzoic acid methyl ester 
• 141544-91-4 1,4-bis(4-hexyloxyphenyl)buta-1,3-diene 
• 1026879-90-2 diethyl (4-hexyloxybenzyl)phosphonate 
• 149365-13-9 diethyl [4-(hexyloxy)benzyl]phosphonate 
• 1058623-61-2 C₃₇H₄₆O₉ 
• 5736-94-7 4-(hexyloxy)benzaldehyde 
• 1372712-87-2 C₂₂H₂₆N₂O₂ 

Relevant academic research and scientific papers

Structure-activity relationship (SAR) studies on the mutagenic properties of 2,7-diaminofluorene and 2,7-diaminocarbazole derivatives

We discovered that 2,7-diaminofluorene or 2,7-diaminocarbazole moiety can be employed as a core structure of highly effective NS5A inhibitors that are connected through amide bonds to proline-valine-carbamate motifs. Amide bonds can be easily cleaved via various metabolic pathways upon administration into the body, and metabolites containing 2,7-diaminofluorene and 2,7-diaminocarbazole core structures have been known to be strong mutagens. To avoid the mutagenesis issue of these core structures, we examined various functional groups at the C9 or N9 position of 2,7-diaminofluorene or 2,7-diaminocarbazole, respectively, through the Ames test in TA98 and TA100 mutants of Salmonella typhimurium LT-2. We discovered that, through proper alkyl substitution at the C9 or N9 position, 2,7-diaminofluorene and 2,7-diaminocarbazole moieties can be successfully employed in drug discovery without necessarily causing mutagenicity problems.

Synthesis of a new triple-responsive biocompatible block copolymer: Self-assembled nanoparticles as potent anticancer drug delivery vehicle

There has been a continuous effort towards a synthesis of new stimuli-responsive polymer nanoparticle systems for improved cancer chemotherapy over the last decade. In this context, we have presently developed a temperature, pH, and redox-responsive amphiphilic block-copolymer capable of forming nanoparticles in the aqueous medium, targeted towards drug delivery applications. The copper-catalyzed azide-alkyne cycloaddition reaction was utilized to tie the ends of two copolymers - a thermo-responsive poly(N-isopropylacrylamide) based copolymer with an azide end group and a pH-responsive hydrophobic polymer with redox responsive disulfide bond and an alkyne end group, producing a new triple responsive amphiphilic block copolymer (PHNP) that self-assemble in water to produce nanoparticles. Upon heating above the cloud point of poly(N-isopropylacrylamide), these nanoparticles experienced further aggregation to produce larger sized particles as measured by dynamic light scattering, UV–visible spectroscopy, and scanning electron microscopy techniques. PHNP was found to be capable of encapsulating drugs like doxorubicin (DOX) and also fluorescent probes alike Nile Red. The drug release kinetics divulged that in a period of 24 h more than 90percent of the encapsulated DOX was released in pH 5.4 buffer having 10 mM glutathione (GSH) at 40 °C, an environment prevailing in cancer tissues. In vitro studies including live-dead assay and rhodamine-DAPI staining showed that PHNP was non-cytotoxic. DOX-loaded PHNP was observed to be more effective in prohibiting bone cancer cell (MG63) line in comparison to free DOX, demonstrated by the significant reduction of IC50 values. The uptake studies showed that DOX-encapsulated PHNP was more effective for morphometric distortion of MG63 cells in comparison to bare DOX. Therefore, the present research on the development of a biocompatible thermal, pH, and redox-responsive polymer opens up new opportunities in the area of polymeric carrier systems for drug delivery to cancer cells.

New convergent one pot synthesis of amino benzyl ethers bearing a nitrogen-containing bicycle

We report herein a new convergent one pot method for the synthesis of amino benzyl ethers containing a bicyclic amine, derived from different substituted benzyl alcohols and bicyclic amino alcohols such as tropine, pseudotropine, and 3-quinuclidinol, using chlorotrimethylsilane and sodium iodide. In order to avoid the competitive reaction with the nitrogen atom, a solution of the separately prepared alkoxide of tropine, pseudotropine, and 3-quinuclidinol was added to the preformed substituted benzyl iodides and allowed to reflux at 90 °C for 15 h under nitrogen atmosphere. This method provides an efficient alternative of the preparation of amino benzyl ethers in organic synthesis with good yields in comparison with existed methods.

CARBAZOLE COMPOUND HAVING ANTI-VIRUS ACTIVITY

The present invention relates to a carbazole compound having anti-virus activity, and more particularly, to a novel compound selected from the group of consisting of a carbazole compound which shows excellent anti-proliferative efficacy against hepatitis C virus (HCV), a pharmaceutically acceptable salt thereof, a hydrate thereof, and an isomer thereof; an anti-virus pharmaceutical composition including the novel compound as an active ingredient; a pharmaceutical composition for preventing or treating liver diseases caused by hepatitis C virus; and a method of preparing the novel compound.

Complexes of borane and N-heterocyclic carbenes: A new class of radical hydrogen atom donor

Calculations suggest that complexes of borane with N-heterocyclic carbenes (NHC) have B-H bond dissocation energies more then 20 kcal/mol less than free borane, diborane, borane-THF, and related complexes. Values are in the range of popular radical hydrogen atom donors like tin hydrides (70-80 kcal/mol). The resulting prediction that NHC borane complexes could be used as radical hydrogen atom donors was verified by radical deoxygenations of xanthates by using either AIBN or triethylborane as initiator. Copyright

Amphiphilic dendritic dipeptides and their self-assembly into helical pores

An amphiphilic dendritic dipeptide, comprises a dipeptide(s) comprising one or more of a naturally occurring or synthetic amino acids and a dendron. These are suitable for use in various formulations, films, coatings, membranes and sensors, among other ap

The application of phenylmethanethiol and benzenethiol derivatives as odorless organosulfur reagents in the synthesis of thiosugars and thioglycosides

p-Octyloxyphenylmethanethiol and p-dodecylbenzenethiol were prepared as new odorless organosulfur reagents. Thiosugars and thioglycosides were synthesized using these reagents without encountering any malodorous procedures.

Molecular Recognition Directed Self-Assembly of Tubular Liquid Crystalline and Crystalline Supramolecular Architectures from Taper Shaped (15-Crown-5)methyl 3,4,5-Tris(p-alkyloxybenzyloxy)benzoates and (15-Crown-5-)methyl 3,4,5-Tris(p-dodecyloxy)benzoate

The syntheses and characterization of a series of (15-crown-5-)methyl 3,4,5-tris(p-alkyloxybenzyloxy)benzoates with alkyl tails of four 25, six 26, and twelve 27 carbon atoms and of (15-crown-5-)methyl 3,4,5-tris(p-dodecyloxybenzoate) 28 are described.Complexation of the crown ether endo-receptor with NaCF3SO3 destabilizes the crystalline phase of 25, 26, 27 and 28 and induces for the case of 27 and 28 the self-assembly of a supramolecular cylindral channel-like architecture which displays a thermotropic hexagonal columnar (Φh) mesophase.Most remarkably, in the crystalline phase of the complexes of 27 with NaCF3SO3 the cylindrical structure of the Φh mesophase is maintained.Characterization of these supramolecular architectures was performed by a combination of differential scanning calorimetry (DSC), thermal optical polarized microscopy, X-ray scattering and molecular modelling.A model is proposed in which a stratum of the column is formed by six molecules of 27 and 28 with the crown ether receptors residing in the column centre and the alkyl tails radiating toward the column periphery. endo-Recognition generated via the (15-crown-5)methyl receptor upon complexation, and exo-recognition provided by the tapered 3,4,5-tris(p-dodecyloxybenzyloxy)benzoate and 3,4,5-tris(p-dodecyloxy)benzoate fragments of 27 and 28 provide the driving force for the self-assembly of this cylindrical supramolecule.

Synthesis of New Liquid Crystalline Compounds based on 1,4-Diarylbuta-1,3-dienes

A group of (E,E)-1,4-diarylbuta-1,3-dienes, substituted in the para-position of one aryl ring by an alkoxy-group and in the para-position of the other aryl group by a cyano- or halogeno-group have been synthesised.The compounds are mesogenic and their phy

New Liquid Crystalline Compounds Based on 1,4-Diarylbuta-1,3-dienes

The first group of fully characterised mesogenic (E,E)-1,4-diarylbuta-1,3-dienes, substituted in the para-position of one aryl ring by an alkoxy-group and in the para-position of the other aryl group by a cyano- or halogeno-group has been prepared by a Wadsworth-Emmons procedure; their physical properties of high birefringence and low viscosity in combination make them particularly suitable for use in liquid crystal display devices when mixed with known liquid crystalline materials.